Waterinsoluble azodyestuffs



Patented Dec. 10, 1935 UNITED STATES PATENT OFFICE WATERINSOLUBLE AZODYESTUFFS of Delaware No Drawing. Application November 6, 1933, figizal No. 696,909. In Germany November 19,

12 Claims.

The present invention relates to new waterinsoluble azodyestufis and to fibre dyed with the said dyestuffs, more particularly it relates to dyestuffs which may be represented by the general formula:

wherein R stands for a radical of the aromatic series, such as a radical of the benzene, naphthalene and anthraquinone series, R stands for a radical of the benzene or naphthalene series, B" stands for alkyl or for a radical of the aromatic series,

wherein R, R and R may bear non-solubilizing v wherein R and R means the same as stated above, and wherein the hydroxy group stands in the 6- or '7-position and the group -R'NHCO in the '7- or 6-position.

Those dyestuffs produced in substance are generally yellow to red to blue to black powders, insoluble in water, suitable for preparing lakes, while those produced on the fibre, especially the cellulosic fibre, according to the usual printing process or according to the method of preparing ice colors, generally yield yellow to red to blue to black shades of goodfastness to light. H

The manufacture of the coupling components used in-the manufacture of my new dyestufis has been described and claimed in my copending application for Letters Patent Serial No. 646,031, filed Dec-ember 6,

The invention illustrated by the following examples, without being limited thereto:

Erample 1.-2 grams of naphtho-7-hydroxy- 6carbonyl-(l-amino-2"-1nethylbenzene) -(1,2, 55-) =2-methylthiazole are dissolved in the usual manner with the aid of caustic soda and some hot water, and the solution is made up with water 1 to one litre. 50 grains of cotton yarn are impregnated in this solution at 30 C. for half an hour, squeezed and, without drying, introduced for about half an hour into one litre of a developing bath prepared in the usual manner from 15 3 grams or" 1,4-diethoxy-2-benzoylamino-5- aminobenz-ene. The cotton is then rinsed, soaped, again rinsed and dried. A greenish-blue of excellent fastness to boiling and light is thus obtained. The dyestuii corresponds to the following for- 20 mula:

CHa

1 N-O-NH-C o-oim 5 CI N CH:

Example 3.- grams of cotton yarn are impregnated as described in Example 1 and introduced for half an hour into one litre of a diazo solution prepared from 2.56 grams of l-methyl- 4 -methoxy- 2 benzoylamino 5 aminobenzene. 5

After rinsing, soaping in a boiling bath, again rinsing and drying, there is obtained a bluishviolet of good fastness to boiling and chlorine and 6'-carbonyl-(l" amino 2" methylbenzene) (1,2',5,4) -2-methy1thiazole of the formula:

excellent fastness to light. The'dyestuff corre- S C OH' sponds to the following formula: 5

( 3H1 HO- N (1)11 ONE-CO.

HN-OC- N=N NHCOCsH:

' yields with diazotized: CH3 8 1-amino-2-chlor0benzene Red CH 1-amino-3-chlorobenzene Red l-amind-Z-nitrobenzene Bluish-red l-amino-Z-methylbenzene Bluishred 15 1-amino-2-methyl-3-chlorobenzene Red Example 4.-2 grams of naphth06 '-hydr0xy- B,rdeaux 7, carbony1 (1,, amm0 2 methylbenzene) 1-am1no-2-methyl-5-ch1orobenzene Bluish-red 2,5,4-)-2-methylthiazole are dissolved in the m ?'m usual manner with the aid of caustic soda and 20 some hot water, and the solution is made up a "BlulshBordea'ux with water to one litre. 50 grams of cotton yarn 'methylazo are impregnated in this solution at 3o-40 c. for F Cwmth half an hour, rinsed and, without drying, introo ydlphenylduced into one litre of a developing bath pre- 4 amine "7"", "Greemsh'blue 5 pared in the usual manner from 3.5 grams of 4-amino-diphenylamine-4"-azo-1-methyl-3"- g 1 amino-4"-methoxybenzene. 'After half an hours enzene "Greems l'blacklsh'blue developing the cotton is rinsed, soaped in a, boil- Example 5 33 4 grams of naphtho-7'-hying bath, again rinsed q'o A greenishdroxy-6-carbonyl-l"-aminonaphthalene-(1'.2-. black of good fastness to mg and chlorine and 5.4-) -2-methylthiaz01e are dissolved in 150 grams excellent fastness 130 light is thus obtained. The of pyridine, Thereto is added, a, diazo solution y t corresponds to the following formu a: which has been prepared from 14.3 grams of 0H; CCl5 1'a CHsO I NH U In an analogous manner cotton impregnated a-naphthylamine. On adding water to the soluaccording to the directions given in paragraph 1 tion, the dyestuff of the formula: of this example yields with diazotized:

1,4-dimethoxy-2-benzoylamino-5- g g aminobenzene Greenish-blue v 5-ch1oro-2-arnino-l-methylbenj I s g cH zene B1uish-red l-amino-Z-chlorobenzene Dull red N 1-amino-3-chlorobenzene Dull red 1-amino-2 -nitrobenzene Bluish-red NH-CO l-amino-3-nitrobenzene Red 1-amino-2.5-dichlorobenzene Bluish-red l-amino-Z-methylbenzene B1uish-red l-amino--nitrobenzene Dull red 1-amino-2-methyl-5-chlorobenzene Bluish-red 3 3 351 1 a g drymg It IS ob- 1-amino-Z-methoxyahnitrobenzene Corinth Example 6 $22; g g g igfgfig gi fig Bluishwiolet' 6'-carbonyl (1" amino 4 methylbenzene) Z'g: (1'.2'.5.4 2-phenylthiazole are dissolved in the diethoxybenzene Green'ish blue usual manner with the aid of caustic soda and &5H T'" some hot water, and the solution is made up with amine V v Bluish grey water to one litre. 50 grams of cotton are imgzagg ggig jgggfif*"' pregnated with this solution for half an hour, Zene v Bluisbblack squeezed and, without drying, introduced for g 'g ;fifii jg g g i '7 about half an hour into a developing bath prechloro s methoxybenzrene Bluish corinth pared 1n the usual manner from 1.47 grams of mchloro-aniline. After rinsing, soaping ina boiling bath, again rinsing and drying, there is obtained a clear reddish-orange. The dyestufi corresponds to the following formula:

HO- N NH- O O I claim: 1. Waterinsoluble azodyestuffs of the general formula:

RHNOO no-iwherein R stands for a radio the aromatic series, R stands for a re naphthale nucleus group -N=N--*t, and ing in orthoqsosming, when produced 0 to blue to black light.

group 1% stand :lroxy group, yieldre, generally yellow of good fastness to 2. Water insoluble azcd estufis of the general formula:

R-HN-OC| N=NR /C RII N wherein R. stands for a radical of the aromatic series, B. stands for a radical of the benzene or naphthalene series, B stands for alkyl or for a radical of the aromatic series, yielding, when produced on the fibre, generally yellow to red to blue to black shades of good fastness to light.

3. Waterinsoluble azodyestufis of the general formula:

wherein R, and R stand for radicals of the benzene or naphthalene series, R. stands for alkyl or for a radical of the benzene or naphthalene series, and wherein R, R and R" may bear substituents selected from the group consisting of alkyl, alkoxy, halogen, the nitro group, an acylamino group and an arylamino group, yielding, when produced on the fibre, generally yellow to red to blue to black shades of good fastness to light.

4. Waterinsoluble azodyestuffs of the general formula:

wherein R and R stand for radicals of the benzene or naphthalene series, and wherein R and R may bear substituents selected from the group consisting of alkyl, alkoxy, halogen, the nitro group, an acylamino group and an arylamino group, yielding, when produced on the fibre, generally yellow to red to blue to black shades of good fastness to light.

5. The waterinsoluble azodyestufi of the following formula:

ll @NHO yielding. when produced on the fibre, red shades of good fastness to light.

6. The waterinsoluble azodyestuff of the following formula: 

